Cyclohexane → HCID 69844880, compound

Temperature

-65 °C

A solution of lithium diisopropylamide-tetrahydrofuran 1.5M solution in cyclohexane (15 mmol, 10 mL) was cooled to −70° C., and a solution of cyclopentane carboxylic acid methyl ester (10 mmol, 1.28 g) in THF (10 mL) was added dropwise over 15 min, maintaining the internal temperature at −60 to −70° C. The yellow solution was stirred 1 h at −70° C. and a solution of 5-iodo-2-pentanone ethylene ketal (10 mmol, 1.28 g) in THF (10 mL) was added over 15 min, while maintaining temperature of −70° C. After srirring for 1 h at −70° C., the reaction mixture was allowed to warm to room temperature overnight. The reaction mixture was poured into brine (150 mL) and the organic layer was separated. The aqueous layer was extracted with ether (20 mL), the combined organic layers were washed with brine (10 mL), dried over anhydrous magnesium sulfate and evaporated to dryness to give 2.5 g (97%) of a pale yellow oil.

1. temperaturewhile maintaining temperature of −70° C
2. waitAfter srirring for 1 h at −70° C.
3. temperatureto warm to room temperature overnight
4. customthe organic layer was separated
5. extractionThe aqueous layer was extracted with ether (20 mL)
6. washthe combined organic layers were washed with brine (10 mL)
7. dry with materialdried over anhydrous magnesium sulfate
8. customevaporated to dryness

ORD record

ord-708c286fa79545abb96c798e7c93f06d

Source dataset

uspto-grants-2004_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06806365B2